Water → HCID 67053845, compound

HRID 2171744Notes

Reaction equation

HRID 2171744 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2([CH3:12])[CH3:11])=[CH:4][C:3]=1[O:13][CH3:14].C([Li])CCC.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:30])(=O)=O)=CC=1.O>C1COCC1>[F:30][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2([CH3:12])[CH3:11])=[CH:4][C:3]=1[O:13][CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 588007N-FluorobenzenesulfonimideHCID 67053816HCID 67053816, compoundHCID 178418339Butyllithium

Product 1

HCID 67053845HCID 67053845, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of 6-bromo-5-methoxy-1,1-dimethyl-indan (2.77 g, 10.8 mmol) (see Example 5) in THF (40 mL) at −78° C. was slowly added n-butyllithium (5.56 ml, 2.5M). The resulting solution was stirred at −78° C. for 0.5 h and a solution of N-fluorobenzenesulfonimide (4.11 g, 13.0 mmol) in THF (40 mL) was added. After an additional 2 h at −78° C., the reaction was warmed to room temperature, poured into water (50 mL), and extracted with ethyl acetate (2×80 mL). The combined organic layers were washed with water (100 mL), dried over sodium sulfate, filtered, and concentrated. Silica gel chromatography (2% ethyl acetate/heptanes) afforded 1.40 g of the title compound as yellow oil.

Workup

  1. customat −78° C.
  2. waitAfter an additional 2 h at −78° C.
  3. temperaturethe reaction was warmed to room temperature
  4. extractionextracted with ethyl acetate (2×80 mL)
  5. washThe combined organic layers were washed with water (100 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7616c63665ca402daa67444fa033d0d9
Source dataset
uspto-grants-2015_06
Patent number
US09051331B2

Reaction notes

Loading…